Pyrroloperimidines or perinones are fused heterocyclic compounds and generally known as basis for various dyes and pigments recommended for wide range of industrial plastics, and synthetic and natural fibers. (e.g. JP 2014214244 A, JP 2013203931 A, JP 2012172070 A, US 20120157586 A1, WO 2008092771 A1) Owing to the highly conjugated structures, these compounds have excellent resistance to heat and light and maintain the brightness of color even under plastic processing or long term sun exposure. Some of them, except bright color, show photoluminescence in short wavelength ranges. (US 2014345195 A1)
The vast majority of the methods reported for synthesis of the perinones are based on condensation of naphthalene-1,8-diamine (NDA) with carboxylic acids or the corresponding anhydrides by refluxing in high boiling solvents or in aggressive acidic media. (e.g. U.S. Pat. No. 5,530,130, U.S. Pat. No. 5,466,805, EP 828,986, U.S. Pat. No. 5,830,931, EP 1,245,645). The reaction proceeds by double cyclization via monoacyl intermediate 1 and the formation of 2-substituted H-perimidine as the most probable product of the first cyclization step.
The arising interest in the perimidine-like structures in the last years has been owned to their possible biological activities. Such various 1- and 2-substituted perimidines have been proposed as anti-fungal, anti-ulcer and anti-tumor agents.
Now then, several documents describe fluorescent dyeing compounds, but not related with the structure of the instant invention's compounds. For example, WO2011054731A1 refers to fluorescent dyes with a POSS domain covalently attached to an organic chromophore domain.
EP1765268 A1, refer to perilene fluorescent compounds useful for hair treatments. Other fluorescent compounds for hair dyes are described in U.S. Pat. No. 7,662,308B2. As far as we know, no perinone compounds even with similar structures have been described as white light emitting molecules in a wide light spectrum.
The 2-substituted perimidines are formed by condensation of NDA not only with acids and their derivatives (anhydrides, acyl chlorides) but with other compounds containing carbonyl group as aldehydes or ketones.
The ring-closure reaction with anhydrides is considered as the best synthetic route because of various reasons: firstly this method allows formation of the product directly in one step in contrast to the reaction with aldehydes or ketones and secondly resulted in the highest yield and less contaminated product in comparison to the reactions with carboxylic acids and acyl chlorides, correspondingly. However, frequently reflux in acetic or trifluoroacetic anhydrides for several hours is needed for the cyclization. Recently, the microwave-assisted synthesis has been developed, which allowed to decrease the reaction time and simultaneously increase the yields with both aliphatic and aromatic acids using high power oven (900 W) (Mobinikhaledi A.; Amrollahi M. A.; Foroughifar N.; Jirandehi H. F. Asian J. Chem. 2005, 17(4), 2411-2414).